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Whether he's doing it on purpose or not, Jake Gyllenhaal is making the Road House press tour all about good, solid clothes. In London a few days ago, he wore a big winter coat by Prada. And in New York City earlier this week, he opted for a navy suit from Wooyoungmi. But during his latest appearance on Good Morning America, the Los Angeles-born actor pulled off his biggest menswear stunt yet – and it's one that, just 10 years ago, was the stuff of nightmares.
No longer! In a Boss blazer, a Calvin Klein white vest, and a pair of Levi's jeans, Gyllenhaal salvaged an unholy trinity into something that felt quietly sick, modern, and throwback all at once. Where blazer-denim combos once flew in the ‘90s, they crumbled when sizing shrunk and Premier League footballers added diamantés. And now, fashion guys like Gyllenhaal are guiding the formerly maligned sequence back into an easier, cooler, loucher place.
How does it work? Well, being an innate fashion guy like Jake Gyllenhaal helps. But it's also because the fit doesn't show off too much. Colours are neutral. The fit doesn't squeeze. It doesn't feel too try-hard. And it also plugs into a wider menswear moment that's been bubbling under for the last couple of years. Marc Jacobs, A$AP Rocky and Austin Butler have all endorsed the combo in the past, and on runways, labels like Ralph Lauren, Drake's and Our Legacy have pushed jeans and blazers. It just has to feel a bit ‘90s, and a bit dad, and you’re good to go.
Elsewhere, it was all killer no filler. This sort of shirt goes with everything. The shoes were Magnanni. The chains were doubled-up to skew sexy without yards of rippling flesh. Gyllenhaal gets it just right.
And so can you. That means taking a deep breath, facing the unknown and pairing a very solid blazer with your very classic jeans.
